Confused yet hopeful

I have a lady that’s 50 yrs old she is good looking she has worked at my shop for five months . All this time she has brought up men she has been with one guy wasn’t able to get it up as she called it and another had a micro penis she had him put it in her ass so could feel something…..She has brought up butt plugs on several occasions in a joking manner. This week my daughter had knee surgery she said when she had her knee done she got so backed up from pain meds that she had to give herself an enema. Is she hinting around and I’m too stupid to see ?

I think she is BEGGING you for some attention. It sounds like she is wanting that attention to be of the anal variety, too!

She is hinting around so much about her back door, I think she wants you to engage more about anal play. You should've asked her if she enjoyed the enema.😉

Is she hinting around and I’m too stupid to see ?

I would say maybe not. In this day and age I wouldn't do anything that you are not 98 percent sure that is what she is "hinting" at. The repercussions can be terrible if HR gets involved. A "he said, she said" scenario has ruined too many reputations in the past.

She may just feel comfortable talking to you in that area of life. She maybe testing how far she can push you. Just be careful in how you go forward in this.

I hope more of you girls chime in

If you’re her boss be VERY careful about getting involved with her. She SOUNDS interested, but if you’re wrong you could lose everything

If you’re her boss be VERY careful about getting involved with her. She SOUNDS interested, but if you’re wrong you could lose everything

And that could be her plan .......

.

Wow! It sounds like it would be fun, but as others have said, BE CAREFUL! BE VERY CAREFUL!!

And I will add, BE EXTREMELY CAREFUL!!!

It could very quickly and easily backfire with a lawsuit, even if everything is consensual.

Even talking about it without acting on it can be sexual harassment.

True, real office romances happen and some work out.

But is it worth the risk?

If anything, I would make sure nothing happens on the work location or or with anything work related.

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Nurse P thanks she is going to buy my business I’m retiring and yes it’s a risk that might be too good to be true. I don’t think she has very good luck with guys. Her dad went from physician to homeless due to addiction her brother is homeless as well mom has plenty of money

Nurse P thanks she is going to buy my business I’m retiring and yes it’s a risk that might be too good to be true. I don’t think she has very good luck with guys. Her dad went from physician to homeless due to addiction her brother is homeless as well mom has plenty of money

In that case I wouldn't do anything until you're retired. I would wait to see how things evolve between you after the power dynamics change. You can stay as close friends and maybe bring up the topic yourself as friends to see her reaction but I wouldn't say or do anything right now.

Be VERY careful. She might want a kinky relationship with you, but she might be trying to lure you into a trap! I agree with @Vzia: wait until you have sold the business, and respond to her in a non-committal manner. If she responds, she's really wanting more. BUT, if she was looking to trap you for personal gain, she no longer has any ammunition.

Whoa. Stop right there.

As the boss and owner, it's your job to set and hold the boundaries. She may be interested, but as many have pointed out, this could end disastrously more easily than happily.

If I were in your position, I'd probably speak to her privately, saying that while you are not personally offended in any way when she tells you about her sex life, butt plugs, anal sex, and enemas, these discussions are not appropriate for the workplace.

Your should also note that they're not appropriate between employer and employee even away from the workplace, as it blurs the boundaries of both your roles. Say, for instance, you were to give her a raise based entirely on her good performance at work. If you and she discuss such personal matters and are ever overheard, there will be charges of favoritism, loss of morale, possibly even people quitting because they don't want to work at a shop where you have to discuss butt sex with the owner to get a raise.

And last, if she still seems to be hinting around, you might remind her there are shops everywhere, you'd be happy to give her a sterling recommendation, and that if she were not your employee you might be interested in further discussion, and who knows where it might lead?

The phrase "Don't shit where you eat" comes to mind.

Dan

Anyone else have a vote

She’s hinting. This could be a trap, an opportunity or she’s simply teasing or she has no motive, just yakking. Be careful, any one of those scenarios could bite you. Shut it down as others have stated.

As several others have stated in so many words, the potential risks outweigh the possible benefits. I understand the temptation, but I wouldn’t give in to it if I were you.

It could be anything - she might be hinting or she might be comfortable discussing things around you without ever thinking these kind of thoughts might come in your mind. So, if you act - you might get lucky or you might get screwed (in the bad sense).

Here's what I would do - in a casual conversation, just tell her you are not the best at reading social cues and prefer people telling you directly what is on their mind (without making reference to anything she might have said. Maybe make up a story where you misjudged what someone meant and ended up having a big laugh when you actually found out). Then let it go - if she wants something more, she will make it evident

Keep it away from the work place and don't fall into possibly being set up for a workplace sexual harrassment law suit. She is far too soon to be trusted with such talk and may view you as prey or future lawsuit cash cow.

I would love to hear how it turns out AFTER she buys your business. I had an almost exact experience, only she was my boss. What she talked about is exactly the same as your 50 year old woman and eventually we ended up in the woods naked. She did not like my performance and as a result she was a B**** to me and made my work a living hell until I found another job in a different city.

There are so many danger signals here. I would stop with her complaining about previous lover's anatomy. This is just awful. This woman is hostile and angry.

If I were you, it's difficult as this is, I would have a talk with her about inappropriate subjects for work and make a note that you did it.

I would listen to everybody here who's telling you to distance yourself from her. I would not even be alone with her again if I were you.

As a former Human Resources professional (as is my wife) I’m firmly in the camp of “can we park this conversation for another time”. Not appropriate now but perhaps later.

Envite her over for dinner at your house leave a combo bag and nozzle hanging from the shower head behind the curtain; when she leaves , check to see if your rig has been messed-with; give it a while ask her over again, if she accepts, Your’er in!….. If she ‘plays … marry her.

Keep us”dry-holes” posted.